


How to Take the Edge Off of the Fear of Flying

by caseyx3lee



Category: Supernatural
Genre: Airports, Anal Fingering, Anal Sex, Blow Jobs, Bottom Dean, CEO!Cas, Hand Jobs, It's a Terrible Life - sort of, M/M, Rimming, business!dean
Language: English
Status: Completed
Published: 2014-09-05
Updated: 2014-09-05
Packaged: 2018-02-16 05:05:35
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,794
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2256903
Author URL: https://archiveofourown.org/users/caseyx3lee/pseuds/caseyx3lee
Summary: <blockquote class="userstuff">
              <p>Dean Winchester hates flying. While taking a bathroom break before his delayed flight home, he decides to have a little fun with another stranded stranger.</p>
            </blockquote>





	How to Take the Edge Off of the Fear of Flying

**Author's Note:**

> Ok, so since I intended this to be one shot, I had/have absolutely no desire or drive to make it longer. It wouldn't be fair to anyone reading because it would be shit quality that I'm forcing to make people happy; and I would hate it. I have no direction for it either. I've turned it back into a one shot for those reasons. I'm working on another (longer) work and will possibly be doing other works once I get back into the swing of writing.
> 
> I apologize to anyone hoping there would be more to this than one single chapter but I don't want to give anyone anything less than my best and as I said, this would not be it.

            “Another delayed flight, awesome,” Dean mumbled to himself. It isn’t the waiting that gets to him, it’s the flying part; Sam always tells him it’s ‘statistically the safest way to travel’ with the worst bitchface possible, he could swear it gets more intense every time. _One more bathroom trip._

            The tiny airport only has single person bathrooms, as if a huge Boeing 747 wasn’t traumatizing enough Dean has been forced to get onto a tiny puddle-jumper connection flight back to Lawrence. As Dean nears the bathrooms he can hear pacing, who ever it is sounds pretty pissed if their rate of footfalls is anything to go by.

            “Hey man, what’s up,” Dean offers the man pacing near the bathrooms, “anyone in there?”

            “No.” He gives it a minute thinking maybe this man will add anything to his previous statement, _more like word_ , and when he doesn’t Dean reaches for the door handle. He’s startled by a very strong grip on his wrist and looks up to be met with the most shockingly blue eyes Dean has ever witnessed. This man is staring at him with such intensity that Dean feels the need to clear his throat, he also wants to straighten his clothes up for some reason; that penetrative gaze is calming while simultaneously being the most terrifying thing Dean has experienced in his 35 years of life, which is saying something. “Would you say I seem overbearing and impatient?”

            This night sure is full of surprises, this man’s voice is impossibly deep and not at all what Dean expected to come out of his mouth.

            “A bit impatient maybe, but I don’t know ya well enough to comment on the overbearing. Do you always approach strangers with a death grip to the wrist?” Dean tried to joke, “If the answer to that is yes, then most women do find that overbearing, or rude.”

            “Not women,” was the only response Dean received. Well, that was also a surprise.

            “Okay, well, I’m gonna hit the head,” _why am I telling him that?_ But just before the door closed Dean could see this stranger eye him up out of the corner of his eye. _Well, fuck it. It’s gonna be a long night, might as well have some fun._ With that thought Dean quickly surveys the area for onlookers and grabs the guy’s hand to pull him into the bathroom with him. The startled little look he receives is all Dean needs to know this was definitely a good idea.

            Once in the small room Dean goes to offer his name, a formality sure, but one he’s gotten into the habit of doing with women, men don’t always care who you are, but before he could get his name out there’s a tongue probing and carefully exploring his mouth while a hand simultaneously ghosts over his ass. _That’s not the way this usually goes,_ not that Dean minds bottoming, he actually likes it on occasion; it’s just been a while since he has, most guys Dean meets tend to be bottoms. Dean is too wrapped up in how passionate this kiss actually is before he realizes that his pants are halfway down his thighs and his hard cock is being spit-wet.

            Dean just leans against the wall and lets this guy go to town on him. There are so many sensations, he’s vaguely aware of a finger tracing his hole lightly while he gets the single best blowjob anyone has ever given.

            “Hey I’m- Nnnggh,” Dean tries to say something as he feels his balls tighten and his climax close, but he is - _rather rudely_ \- interrupted by two of the most magical fingers Dean has ever felt inside him; and as soon as those spit slick - _how did that happen? Hell, **when** did that happen?-_ breach his entrance he looses his very light finger hold on his control and empties his admittedly overfull balls into this guys mouth. The stranger moans around his dick in the process as if it’s the best thing he’s ever tasted, if Dean wasn’t so spent that sound and the feeling of having his dick hummed around would have him hard again.

            “My turn,” and before Dean can respond or even reach his hand down to undo this man’s pants he’s being pushed face first into the bathroom wall.

            “Whoa buddy,” Dean says while rubbing his now bare ass cheeks against his growing erection since he feels him pull away at the inflection in his voice that clearly sounds like ‘I’m not into it,’ “it’s just been a while so you’ll have to go kinda slow,” Dean feels a little sheepish saying it, it’s not the he minds, he just hasn’t had time for any fun lately.

            “I can manage that.” _The depth of this guys voice should be illegal._ Dean can feel his dick trying in vain to stand at attention at that voice alone. He lets slip a small moan, or maybe it’s more of a whimper, but he doesn’t have time to dwell on the sounds he’s making because next thing he knows this generous stranger is on his knees again, only this time he’s behind Dean. He can feel a finger gently massaging his hole while he feels another hand gently cupping his balls. _So much for being done_ , Dean can feel his cock hardening at all the attention and sensations. The wet, warm feeling of a tongue circling his entrance surprises him, then he feels a wet finger slip in, then two fingers are slowly sliding in and out while scissoring Dean open.

            While Dean is lost to the sensations, and the probably too loud moans escaping him, he feels a hand wrap around his half hard dick and stroke him slowly, in time with the now three, slow masterful fingers fucking into his ass. When he feels those wonderful finger slide out he’s pretty sure he whimpers at the empty feeling he’s left with.

            “Shh, don’t whine,” it’s soothing, yet firm; and incredibly close to his ear which this man with magic fingers bites. While still stroking Dean’s hard dick rhythmically and nibbling his ear he feels the head of a rather large dick against his hole, before Dean can say anything about his size this man is slowly pushing in. Once he bottoms out, which takes a decent amount of time, he let’s Dean adjust. He shows amazing restraint by staying completely still until Dean becomes restless and starts slowly grinding on his dick. Dean’s airport fuck takes this to mean that he’s free to move now and grabs Deans’ wrists with one hand, pinning them to his back, while stroking his hard cock tight and fast while fucking into his tight ass at the same, agonizingly commendable pace.

            Dean is vaguely aware of the very loud and rather unmanly sounds escaping him, with every thrust his prostate is hit and he is helpless to stop the things coming out of him. “Yeah, you fuck my tight hole- ah YESS,” then more moaning. He is pretty sure the entire airport knows what is happening inside this bathroom but he doesn’t give a shit because he hasn’t been fucked so good in a very long time. “Oh God, I’m gonna-“

            “Don’t.” One word, and no more thrusting.  Dean tries to wiggle around on his dick a little, searching for any friction on any part of his burning body. This man has taken him apart hard and fast, and now has his thumb and forefinger wrapped tightly around the base of Dean’s cock to hold him off while pinning him unable to move against the wall of the bathroom. “I’m not finished with you yet,” and with that the stranger resumes his thrusting/stroking combination, only instead of a pounding fastness it’s excruciatingly slow. Instead of the loud, ok screams, coming out Dean, he is now moaning, low and loud. “That’s much better isn’t it? You enjoy my cock in your ass?” _God, that VOICE._

            “Oh, yeah baby, you fuck me so good.”

            “Cum for me.” It’s almost a whisper, and as soon as he hears the words Dean does. He falls right over that edge he had been dangling on and as he dumps a second load onto this man’s hand and the wall he can feel the other’s dick stiffen that little bit more and then pulse as it’s contents are emptied into Dean’s ass.

            Dean isn’t too sure but he thinks he feels lips brush the back of his neck.

            Once they’re cleaned up and fully clothed again Dean can’t help but hope maybe this man will live relatively close to Northern California, “So, where are you headed?”

            “Back to New York, Manhattan to be precise,” he says as he buttons his pants, “and you?”

            “Nor Cal. Got family out there. You live in the City?”

            “Yeah, for now.” He doesn’t look particularly thrilled about it, but he must have a decent job if he can afford it. Dean pouts inwardly at the extreme amount of distance between him and the best lay he’s ever had.

            “Well, have a safe trip home…?” He holds his hand out and waits for name. He gets a smirk and handshake in return, _well that was rude._

            Then he exits the bathroom. Dean counts to twenty-five and then exits as well, Handsome Stranger is nowhere to be seen, _probably near the other end of the tiny airport by now._

            “Now boarding flight 2 2 6 5, gate C. Flight 2 2 6 5, gate C all passengers.”

            Dean vaguely hopes that his stranger hadn’t missed his flight. As he boards his plane his heart starts to race and he can feel his palms sweating. Dean makes his way to his seat and starts to try and calm his breathing while reaching into his bag for his trusty flight companion, his iPod loaded with all of his classic rock and his latest birthday present from Sam, a pair of Beats Studio noise cancelling headphones. Sam knows he hates to fly and bought the headphones as a way to help distract and comfort Dean on the many business trips he has to take. As he digs for the wire in the little pocket he usually keeps them in in his laptop bag he feels a paper in with it. _Huh, that’s weird._ Mostly because Dean is an organized freak about travelling, _surprising to most I know,_ and he wouldn’t put paper in that pocket, actually can’t remember putting paper in that pocket.

            His confusion is erased as soon as he pulls it out and opens the small slip. Written in neat script is a note and telephone number.

If you’re ever in New York, call me. (212)665-4363 Castiel


End file.
